JPS6127362B2 - - Google Patents
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- Publication number
- JPS6127362B2 JPS6127362B2 JP5208983A JP5208983A JPS6127362B2 JP S6127362 B2 JPS6127362 B2 JP S6127362B2 JP 5208983 A JP5208983 A JP 5208983A JP 5208983 A JP5208983 A JP 5208983A JP S6127362 B2 JPS6127362 B2 JP S6127362B2
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- JP
- Japan
- Prior art keywords
- group
- mixture
- reduced pressure
- under reduced
- formula
- Prior art date
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- 150000001875 compounds Chemical class 0.000 claims description 16
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 239000005645 nematicide Substances 0.000 claims description 4
- 239000000460 chlorine Substances 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 239000004480 active ingredient Substances 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 125000005504 styryl group Chemical group 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 21
- 238000004519 manufacturing process Methods 0.000 description 15
- 239000000203 mixture Substances 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 239000000243 solution Substances 0.000 description 10
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
- 241000244206 Nematoda Species 0.000 description 6
- 230000001069 nematicidal effect Effects 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- 230000003197 catalytic effect Effects 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
- 235000017557 sodium bicarbonate Nutrition 0.000 description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- UORVCLMRJXCDCP-UHFFFAOYSA-N propynoic acid Chemical class OC(=O)C#C UORVCLMRJXCDCP-UHFFFAOYSA-N 0.000 description 3
- CIFFBTOJCKSRJY-UHFFFAOYSA-N 3α,4,7,7α-tetrahydro-1h-isoindole-1,3(2h)-dione Chemical compound C1C=CCC2C(=O)NC(=O)C21 CIFFBTOJCKSRJY-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- 206010020649 Hyperkeratosis Diseases 0.000 description 2
- 241000193977 Pratylenchus musicola Species 0.000 description 2
- 150000000475 acetylene derivatives Chemical class 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 239000002917 insecticide Substances 0.000 description 2
- XNERWVPQCYSMLC-UHFFFAOYSA-N phenylpropiolic acid Chemical compound OC(=O)C#CC1=CC=CC=C1 XNERWVPQCYSMLC-UHFFFAOYSA-N 0.000 description 2
- -1 polyoxyethylene Polymers 0.000 description 2
- 235000013311 vegetables Nutrition 0.000 description 2
- FNZSVEHJZREFPF-SSDOTTSWSA-N (2r)-2-pentylbutanedioic acid Chemical compound CCCCC[C@@H](C(O)=O)CC(O)=O FNZSVEHJZREFPF-SSDOTTSWSA-N 0.000 description 1
- HUWSZNZAROKDRZ-RRLWZMAJSA-N (3r,4r)-3-azaniumyl-5-[[(2s,3r)-1-[(2s)-2,3-dicarboxypyrrolidin-1-yl]-3-methyl-1-oxopentan-2-yl]amino]-5-oxo-4-sulfanylpentane-1-sulfonate Chemical compound OS(=O)(=O)CC[C@@H](N)[C@@H](S)C(=O)N[C@@H]([C@H](C)CC)C(=O)N1CCC(C(O)=O)[C@H]1C(O)=O HUWSZNZAROKDRZ-RRLWZMAJSA-N 0.000 description 1
- PAAZPARNPHGIKF-UHFFFAOYSA-N 1,2-dibromoethane Chemical compound BrCCBr PAAZPARNPHGIKF-UHFFFAOYSA-N 0.000 description 1
- KNKRKFALVUDBJE-UHFFFAOYSA-N 1,2-dichloropropane Chemical compound CC(Cl)CCl KNKRKFALVUDBJE-UHFFFAOYSA-N 0.000 description 1
- YHRUOJUYPBUZOS-UHFFFAOYSA-N 1,3-dichloropropane Chemical compound ClCCCCl YHRUOJUYPBUZOS-UHFFFAOYSA-N 0.000 description 1
- SZIFAVKTNFCBPC-UHFFFAOYSA-N 2-chloroethanol Chemical compound OCCCl SZIFAVKTNFCBPC-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- QCFYJCYNJLBDRT-UHFFFAOYSA-N Bis(2-chloro-1-methylethyl)ether Chemical compound ClCC(C)OC(C)CCl QCFYJCYNJLBDRT-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 240000000249 Morus alba Species 0.000 description 1
- 235000008708 Morus alba Nutrition 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 244000269722 Thea sinensis Species 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000003899 bactericide agent Substances 0.000 description 1
- GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 1
- LUEHNHVFDCZTGL-UHFFFAOYSA-N but-2-ynoic acid Chemical compound CC#CC(O)=O LUEHNHVFDCZTGL-UHFFFAOYSA-N 0.000 description 1
- LDVVMCZRFWMZSG-UHFFFAOYSA-N captan Chemical compound C1C=CCC2C(=O)N(SC(Cl)(Cl)Cl)C(=O)C21 LDVVMCZRFWMZSG-UHFFFAOYSA-N 0.000 description 1
- 239000000073 carbamate insecticide Substances 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 235000011089 carbon dioxide Nutrition 0.000 description 1
- LFHISGNCFUNFFM-UHFFFAOYSA-N chloropicrin Chemical compound [O-][N+](=O)C(Cl)(Cl)Cl LFHISGNCFUNFFM-UHFFFAOYSA-N 0.000 description 1
- CRQQGFGUEAVUIL-UHFFFAOYSA-N chlorothalonil Chemical compound ClC1=C(Cl)C(C#N)=C(Cl)C(C#N)=C1Cl CRQQGFGUEAVUIL-UHFFFAOYSA-N 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- KQTVWCSONPJJPE-UHFFFAOYSA-N etridiazole Chemical compound CCOC1=NC(C(Cl)(Cl)Cl)=NS1 KQTVWCSONPJJPE-UHFFFAOYSA-N 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- KGVPNLBXJKTABS-UHFFFAOYSA-N hymexazol Chemical compound CC1=CC(O)=NO1 KGVPNLBXJKTABS-UHFFFAOYSA-N 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 150000001247 metal acetylides Chemical class 0.000 description 1
- AFCCDDWKHLHPDF-UHFFFAOYSA-M metam-sodium Chemical compound [Na+].CNC([S-])=S AFCCDDWKHLHPDF-UHFFFAOYSA-M 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- UMIPWJGWASORKV-UHFFFAOYSA-N oct-1-yne Chemical compound CCCCCCC#C UMIPWJGWASORKV-UHFFFAOYSA-N 0.000 description 1
- 239000002420 orchard Substances 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- LKPLKUMXSAEKID-UHFFFAOYSA-N pentachloronitrobenzene Chemical compound [O-][N+](=O)C1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl LKPLKUMXSAEKID-UHFFFAOYSA-N 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical compound CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Landscapes
- Agricultural Chemicals And Associated Chemicals (AREA)
Description
近年、農作物に対する植物寄生性線虫が生産阻
害の大きな要因として注目され、特に野菜の指定
生産地制度等、園芸作物の振興による野菜の種類
の増加と連作により、線虫の被害が年々増加の傾
向にある。さらに、果樹園、茶園、桑園等の永年
作物が不可能であり、線虫は重要な生産阻害因子
となつている。
本発明者らは、以上のような視点から安全でし
かも有効な殺線虫剤を見出すべく種々検討の結
果、アセチレン誘導体である一般式がR1−Ｃ≡
Ｃ−COOR2〔式中R1は水素原子、炭素原子数１
〜６のアルキル基、CH2＝CH−、CH2＝Ｃ
（CH3）−、
In recent years, plant-parasitic nematodes have attracted attention as a major factor that inhibits production of agricultural crops.In particular, with the increase in the variety of vegetables and continuous cultivation due to the promotion of horticultural crops, such as the designated production area system for vegetables, nematode damage is increasing year by year. There is a tendency. Furthermore, it is impossible to grow perennial crops in orchards, tea gardens, mulberry gardens, etc., and nematodes are an important factor inhibiting production. As a result of various studies to find a safe and effective nematocide from the above viewpoint, the present inventors found that the general formula of an acetylene derivative is R 1 -C≡
C-COOR 2 [In the formula, R 1 is a hydrogen atom, the number of carbon atoms is 1
~6 alkyl groups, CH2 =CH-, CH2 =C
( CH3 )−,
【式】CH3−CH
＝CH−、CH3（CH＝CH）2−、CH≡Ｃ（CH2）6
−、C4H9C≡Ｃ−、HOOC−（CH2）o−（ｎは１〜
８の整数を表わす）、CH3OOC−Ｃ≡Ｃ−、
HOOC−Ｃ≡Ｃ（CH2）6−、CH3OOC−Ｃ≡Ｃ
（CH2）6−、スチリル基、または塩素原子、ニト
ロ基またはメトキシ基でモノ置換されてもよいフ
エニル基を表わし、R2は水素原子、炭素原子数
１〜８のアルキル基、−CH2CH2Cl、−CH2CH＝
CH2または−CH2CH2N（C2H5）2を表わす〕
で表わされる化合物群の浸漬法における殺線虫試
験で高い効果を有することを見出し、本発明を完
成させた。
次に本発明に係る化合物類を第１表に例示する
が、第１表に例示した化合物は本発明に係るアセ
チレン類の種類を限定するものではない。
本発明に係る化合物は一般に次の様にして製造
することが出来る既知化合物群である。
本発明に係るアセチレンモノカルボン酸類であ
るプレピオール酸およびその誘導体は金属アセチ
リドと二酸化炭素を反応させて容易に合成するこ
とができる。
〔J.H.Wotlz、E.S.Hudak、J.Org.Chem.19、
1580（1954）〕[Formula] CH 3 −CH = CH−, CH 3 (CH=CH) 2 −, CH≡C(CH 2 ) 6
−, C 4 H 9 C≡C−, HOOC− (CH 2 ) o − (n is 1 to
(representing an integer of 8), CH 3 OOC−C≡C−,
HOOC−C≡C(CH 2 ) 6 −, CH 3 OOC−C≡C
( CH2 ) 6- , a styryl group, or a phenyl group which may be monosubstituted with a chlorine atom, a nitro group or a methoxy group, and R2 is a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, -CH2 CH 2 Cl, −CH 2 CH=
CH 2 or -CH 2 CH 2 N(C 2 H 5 ) 2 ] was found to have a high effect in a nematicidal test using the immersion method, and the present invention was completed. Next, the compounds according to the present invention are illustrated in Table 1, but the compounds illustrated in Table 1 do not limit the types of acetylenes according to the present invention. The compounds according to the present invention are a group of known compounds that can generally be produced in the following manner. Prepiolic acid and its derivatives, which are acetylene monocarboxylic acids according to the present invention, can be easily synthesized by reacting metal acetylide and carbon dioxide. [JHWotlz, ESHudak, J.Org.Chem. 19 ,
1580 (1954)]
【表】【table】
【表】【table】
【表】
製造例 １
化合物番号４の化合物の製法
プロピオール酸7.0ｇ（0.1mole）、２−クロル
エタノール12.1ｇ（0.15mole）、ベンゼン100mlの
混合物に触媒量のパラトルエンスルホン酸を加
え、デイーンスタークの水分離器を用い、水がほ
とんど分離しなくなるまで還流した。放冷後、反
応液を重炭酸ナトリウム水溶液で洗浄、水洗後、
無水硫酸ナトリウムで乾燥してから、ベンゼン減
圧留去し、残留物を減圧蒸留した。
表題化合物４が9.8ｇ得られた。bp65〜67℃／
26mmHg、収率74％
製造例 ２
化合物番号５の化合物の製法
プロピオール酸20ｇ（0.29mole）、イソプタノ
ール40ｇおよびベンゼン100mlの混合物に触媒量
のパラトルエンスルホン酸を加え、6.5時間デイ
ーン−スターク（Dean−Stark）水分離器を用い
て還流した。
放冷後、水で希釈して有機層を分離した。これ
を重炭酸ナトリウム水溶液で洗い、無水硫酸ナト
リウムで乾燥してから減圧濃縮し、反応混合物18
ｇを得た。
これを減圧蒸留し、17ｇの目的物を得た（収率
47％）。bp152℃
製造例 ３
化合物番号９の化合物の製法
メチルプロピオール酸8.4ｇ（0.1mole）、エタ
ノール9.2ｇ、ベンゼン200mlの溶液に触媒量のパ
ラトルエンスルホン酸を加え、デイーンスターク
水分離器を用い、ほとんど水が分離しなくなるま
で還流した。
放冷後、反応液を重炭酸ナトリウム水溶液で洗
浄、水洗後、無水硫酸ナトリウムで乾燥してから
ベンゼン減圧留去し、残留物を減圧蒸留した。表
題化合物９が7.5ｇ得られた。bp160〜161℃／730
mmHg収率66.9％
製造例 ４
化合物番号21の化合物の製法
ナトリウムアミド50ｇ（1.28mole）の無水エー
テル１懸濁液に１−オクチン142ｇ
（1.29mole）を激しいアンモニア発生を保つよう
に加えてから４時間かきまぜ還流した。ガス発生
が非常に遅くなつてから混合物を粉砕ドライアイ
ス１Kg上に注ぎ一夜放置した。
塩化アンモニウム飽和水溶液で分解し、常法通
り後処理した。減圧蒸留によりノニン酸を得た。
収量107ｇ（収率54％）。bp122℃／2.2mmHg
製造例 ５
化合物番号39の化合物の製法
常法により、ジアゾメタンを用いてフエニルプ
ロピオール酸をメチル化し、メチルエステルを定
量的に得た。
bp120℃／８mmHg
製造例 ６
化合物番号40の化合物の製法
フエニルプロピオール酸14.6ｇ（0.1mole）、エ
タノール9.2ｇ、ベンゼン200mlの混合物に触媒量
のパラトルエンスルホン酸を加え、デイーンスタ
ーク水分離器を用い、水がほとんど分離しなくな
るまで還流した。放冷後、反応液を重炭酸ナトリ
ウム水溶液で洗い、水洗後、無水硫酸ナトリウム
で乾燥してからベンゼン減圧留去し、残留物を減
圧蒸留した。表題化合物40が12.8ｇ得られた。
bp124℃／６mmHg収率73.5％
本発明組成物の有効成分化合物は必要によりペ
ンタクロルニトロベンゼン（PCNB）、ビス（ジ
メチルチオカルバモイル）ジスルフイド、テトラ
クロルイソフタロニトリル、３−ヒドロキシ−５
−メチルイソオキサゾール、５−エトキシ−３−
トリクロルメチル−１・２・４−チアジアゾー
ル、Ｎ−（トリクロルメチルチオ）−４−シクロヘ
キセン−１・２−ジカルボキシイミド、Ｎ−
（１・１・２・２・−テトラクロルエチルチオ）−
４−シクロヘキセン−１・２−ジカルボキシイミ
ド、クロルピクリン等の殺菌剤や、１・２−ジブ
ロムエタン、１・３−ジクロルプロパンおよび
１・２−ジクロルプロパン、ビス（２−クロロ−
１−メチルエチル）−エーテル、ブロモメタン、
Ｎ−メチルジチオカルバミン酸ナトリウム（アン
モニウム）等の殺線虫剤や有機燐系殺虫剤、カー
バメイト系殺虫剤、塩素系殺虫剤または各種除草
剤、肥料質類と混合して、或いは混合剤として使
用することも可能である。
つぎに本発明の殺線虫剤の効果を試験例によつ
て示す。
試験例 １
供試線虫は、アルフアルフアのカルスにより室
内培養したミナミネグサレセンチユウ
（Pratylenchus Coffeae）である。各薬剤を１％
濃度になるようにメタノールに溶解し、これを
0.1％EPAN420（ポリオキシエチレンポリプロピ
レングライコール）水溶液で希釈して所定の濃度
とした。
各希釈液を10mlづつシラキウス時計皿に分注
し、線虫を時計皿当り150〜200頭入れ、暗黒下25
℃で48時間生育管理した。
その後、双眼顕微鏡下で生死を調査して殺線虫
率を求めた。試験は５回くり返して実施した。そ
の結果は第２表に示す通りである。[Table] Production Example 1 Production of Compound No. 4 A catalytic amount of para-toluenesulfonic acid was added to a mixture of 7.0 g (0.1 mole) of propiolic acid, 12.1 g (0.15 mole) of 2-chloroethanol, and 100 ml of benzene. The mixture was refluxed using a Stark water separator until almost no water separated. After cooling, the reaction solution was washed with an aqueous sodium bicarbonate solution, and then washed with water.
After drying over anhydrous sodium sulfate, benzene was distilled off under reduced pressure, and the residue was distilled under reduced pressure. 9.8g of title compound 4 was obtained. bp65~67℃/
26 mmHg, yield 74% Production Example 2 Method for producing Compound No. 5 A catalytic amount of para-toluenesulfonic acid was added to a mixture of 20 g (0.29 mole) of propiolic acid, 40 g of isoptanol, and 100 ml of benzene, and the Dean-Stark (Dean) -Stark) was refluxed using a water separator. After cooling, it was diluted with water and the organic layer was separated. This was washed with an aqueous sodium bicarbonate solution, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to give a reaction mixture of 18
I got g. This was distilled under reduced pressure to obtain 17 g of the target product (yield:
47%). bp152℃ Production Example 3 Method for producing compound No. 9 Add a catalytic amount of para-toluenesulfonic acid to a solution of 8.4 g (0.1 mole) of methylpropiolic acid, 9.2 g of ethanol, and 200 ml of benzene, and use a Dean Stark water separator. , and refluxed until almost no water separated. After cooling, the reaction solution was washed with an aqueous sodium bicarbonate solution, washed with water, dried over anhydrous sodium sulfate, and then benzene was distilled off under reduced pressure, and the residue was distilled under reduced pressure. 7.5 g of the title compound 9 was obtained. bp160-161℃/730
mmHg yield 66.9% Production example 4 Method for producing compound No. 21 142 g of 1-octyne in 1 suspension of anhydrous ether of 50 g (1.28 mole) of sodium amide
(1.29 mole) was added to maintain vigorous ammonia generation, and the mixture was stirred and refluxed for 4 hours. Once gas evolution had slowed down considerably, the mixture was poured onto 1 kg of crushed dry ice and left overnight. The mixture was decomposed with a saturated aqueous ammonium chloride solution and worked up in a conventional manner. Nonic acid was obtained by distillation under reduced pressure.
Yield 107g (yield 54%). bp122°C/2.2mmHg Production Example 5 Production of Compound No. 39 Phenylpropiolic acid was methylated using diazomethane by a conventional method to quantitatively obtain methyl ester. bp120℃/8mmHg Production Example 6 Production of Compound No. 40 A catalytic amount of para-toluenesulfonic acid was added to a mixture of 14.6g (0.1mole) of phenylpropiolic acid, 9.2g of ethanol, and 200ml of benzene, followed by Dean Stark water separation. The mixture was refluxed using a vessel until almost no water separated. After cooling, the reaction solution was washed with an aqueous sodium bicarbonate solution, washed with water, dried over anhydrous sodium sulfate, and then benzene was distilled off under reduced pressure, and the residue was distilled under reduced pressure. 12.8g of the title compound 40 was obtained.
bp124℃/6mmHgYield 73.5% The active ingredient compounds of the composition of the present invention may optionally include pentachlornitrobenzene (PCNB), bis(dimethylthiocarbamoyl)disulfide, tetrachloroisophthalonitrile, 3-hydroxy-5
-methylisoxazole, 5-ethoxy-3-
Trichloromethyl-1,2,4-thiadiazole, N-(trichloromethylthio)-4-cyclohexene-1,2-dicarboximide, N-
(1,1,2,2-tetrachloroethylthio)-
Bactericidal agents such as 4-cyclohexene-1,2-dicarboximide, chloropicrin, 1,2-dibromoethane, 1,3-dichloropropane, 1,2-dichloropropane, bis(2-chloro-
1-methylethyl)-ether, bromomethane,
Mix with nematicides such as sodium N-methyldithiocarbamate (ammonium), organophosphorus insecticides, carbamate insecticides, chlorine insecticides, various herbicides, fertilizers, or use as a mixture. It is also possible. Next, the effects of the nematocide of the present invention will be shown using test examples. Test Example 1 The test nematode is Pratylenchus Coffeae, which was cultured indoors using alpha alpha callus. 1% of each drug
Dissolve in methanol to a certain concentration, and add this to
It was diluted with a 0.1% EPAN420 (polyoxyethylene polypropylene glycol) aqueous solution to a predetermined concentration. Dispense 10 ml of each diluted solution into a Syracius watch glass, add 150 to 200 nematodes per watch glass, and place in the dark for 25 minutes.
Growth was controlled at ℃ for 48 hours. Thereafter, the nematocidal rate was determined by examining whether they were alive or dead under a binocular microscope. The test was repeated five times. The results are shown in Table 2.
【表】【table】
【表】
試験例 ２
試験例１と同様にアルフアルフアのカルスによ
り室内培養したミナミネグサレセンチユウ
（Pratylenchus Coffeae）を使用した。各検定薬
剤は20％乳剤に調製して使用した。製剤の内容は
本発明に使用する各化合物20重量部、キシレン70
重量部およびポリオキシエチレンノニルフエニル
エーテル10重量部を混合して乳剤とした。本製剤
を水で希釈して所定の濃度とした。各希釈液を10
mlづつシラキウス時計皿に分注し、線虫を時計皿
当り150〜200頭入れ、暗黒下25℃で48時間生育管
理した。
その後、双眼顕微鏡下で生死を調整して殺線虫
率を求めた。試験は５回くり返し実施した。その
結果は第３表に示す通りである。[Table] Test Example 2 As in Test Example 1, Pratylenchus Coffeae, which was cultivated indoors using alpha alpha callus, was used. Each test drug was prepared into a 20% emulsion and used. The contents of the preparation are 20 parts by weight of each compound used in the present invention, and 70 parts by weight of xylene.
Parts by weight and 10 parts by weight of polyoxyethylene nonyl phenyl ether were mixed to prepare an emulsion. This formulation was diluted with water to the desired concentration. 10 of each dilution
Each ml was dispensed into a Syracius watch glass, 150 to 200 nematodes were placed in each watch glass, and growth was controlled in the dark at 25°C for 48 hours. Thereafter, the nematocidal rate was determined by adjusting for live and dead under a binocular microscope. The test was repeated five times. The results are shown in Table 3.
【表】【table】
Claims (1)
ル基、CH2＝CH−、CH2＝Ｃ（CH3）−、
【式】CH3−CH＝CH−、 CH3（CH＝CH）2−、CH≡Ｃ（CH2）6−、C4H9C
≡Ｃ−、HOOC−（CH2）o−（ｎは１〜８の整数を
表わす）、CH3OOC−Ｃ≡Ｃ−、HOOC−Ｃ≡Ｃ
（CH2）6−、CH3OOC−Ｃ≡Ｃ（CH2）6−、スチ
リル基、または塩素原子、ニトロ基またはメトキ
シ基でモノ置換されていてもよいフエニル基を表
わし、R2は水素原子、炭素原子数１〜８のアル
キル基、−CH2CH2Cl、−CH2CH＝CH2または−
CH2CH2N（C2H5）2を表わす〕で表わされる化合
物群から選ばれる少くとも一種または二種以上の
化合物を有効成分として含有することを特徴とす
る殺線虫剤。[Claims] 1 General formula R 1 -C≡C-COOR 2 [In the formula, R 1 is a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, CH 2 =CH-, CH 2 =C (CH 3 )−,
[Formula] CH 3 −CH=CH−, CH 3 (CH=CH) 2 −, CH≡C(CH 2 ) 6 −, C 4 H 9 C
≡C-, HOOC-(CH 2 ) o - (n represents an integer from 1 to 8), CH 3 OOC-C≡C-, HOOC-C≡C
( CH2 ) 6- , CH3OOC -C≡C( CH2 ) 6- , a styryl group, or a phenyl group which may be monosubstituted with a chlorine atom, a nitro group or a methoxy group, and R2 is hydrogen. atom, alkyl group having 1 to 8 carbon atoms, -CH 2 CH 2 Cl, -CH 2 CH=CH 2 or -
A nematicide characterized by containing as an active ingredient at least one or more compounds selected from the group of compounds represented by CH 2 CH 2 N (representing C 2 H 5 ) 2 .
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5208983A JPS58174302A (en) | 1983-03-28 | 1983-03-28 | Nematocide |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5208983A JPS58174302A (en) | 1983-03-28 | 1983-03-28 | Nematocide |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP55027156A Division JPS6011882B2 (en) | 1980-03-04 | 1980-03-04 | Nematicide |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS58174302A JPS58174302A (en) | 1983-10-13 |
| JPS6127362B2 true JPS6127362B2 (en) | 1986-06-25 |
Family
ID=12905097
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP5208983A Granted JPS58174302A (en) | 1983-03-28 | 1983-03-28 | Nematocide |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS58174302A (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4898853A (en) * | 1988-02-16 | 1990-02-06 | Merck & Co. Inc. | Acetylenic esters |
| US5502242A (en) * | 1993-08-06 | 1996-03-26 | Sumitomo Chemical Company, Limited | Propiolate ester compound an acaricide containing the same as an active ingredient and an acaricidal method |
-
1983
- 1983-03-28 JP JP5208983A patent/JPS58174302A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS58174302A (en) | 1983-10-13 |
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