JPS6124361B2 - - Google Patents
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- Publication number
- JPS6124361B2 JPS6124361B2 JP50034586A JP3458675A JPS6124361B2 JP S6124361 B2 JPS6124361 B2 JP S6124361B2 JP 50034586 A JP50034586 A JP 50034586A JP 3458675 A JP3458675 A JP 3458675A JP S6124361 B2 JPS6124361 B2 JP S6124361B2
- Authority
- JP
- Japan
- Prior art keywords
- compounds
- compound
- carrier
- weight
- barley
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 150000001875 compounds Chemical class 0.000 claims description 29
- 235000007320 Avena fatua Nutrition 0.000 claims description 15
- 239000000203 mixture Substances 0.000 claims description 13
- 230000002363 herbicidal effect Effects 0.000 claims description 12
- 244000075850 Avena orientalis Species 0.000 claims description 10
- 235000005373 Uvularia sessilifolia Nutrition 0.000 claims description 10
- 235000013339 cereals Nutrition 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 5
- 229910052731 fluorine Chemical group 0.000 claims description 5
- 239000011737 fluorine Chemical group 0.000 claims description 5
- 239000004094 surface-active agent Substances 0.000 claims description 5
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 239000000460 chlorine Substances 0.000 claims description 3
- 239000004480 active ingredient Substances 0.000 claims description 2
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 125000001153 fluoro group Chemical group F* 0.000 claims description 2
- 241000209219 Hordeum Species 0.000 description 10
- 235000007340 Hordeum vulgare Nutrition 0.000 description 10
- 239000003795 chemical substances by application Substances 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 231100000614 poison Toxicity 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- 241000209764 Avena fatua Species 0.000 description 5
- 239000000654 additive Substances 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- -1 sulfuric acid Chemical class 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 235000004535 Avena sterilis Nutrition 0.000 description 4
- 241000196324 Embryophyta Species 0.000 description 4
- 239000002270 dispersing agent Substances 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 239000002574 poison Substances 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 239000003381 stabilizer Substances 0.000 description 4
- 231100000674 Phytotoxicity Toxicity 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 239000012141 concentrate Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- 239000004009 herbicide Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 239000000428 dust Substances 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 230000007096 poisonous effect Effects 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000002689 soil Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000004546 suspension concentrate Substances 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 239000004563 wettable powder Substances 0.000 description 2
- 239000000080 wetting agent Substances 0.000 description 2
- SZIFAVKTNFCBPC-UHFFFAOYSA-N 2-chloroethanol Chemical compound OCCCl SZIFAVKTNFCBPC-UHFFFAOYSA-N 0.000 description 1
- QRANPOAGRHSSMN-UHFFFAOYSA-N 2-chloroethyl 2-(N-benzoyl-3,4-dichloroanilino)propanoate Chemical compound C(C1=CC=CC=C1)(=O)N(C(C(=O)OCCCl)C)C1=CC(=C(C=C1)Cl)Cl QRANPOAGRHSSMN-UHFFFAOYSA-N 0.000 description 1
- FYTQLMHHVHDTRJ-UHFFFAOYSA-N 2-chloroethyl 2-(N-benzoyl-3-chloro-4-fluoroanilino)propanoate Chemical compound C(C1=CC=CC=C1)(=O)N(C(C(=O)OCCCl)C)C1=CC(=C(C=C1)F)Cl FYTQLMHHVHDTRJ-UHFFFAOYSA-N 0.000 description 1
- UKDPYBMPYKTMND-UHFFFAOYSA-N 2-chloroethyl 2-(N-benzoyl-4-fluoroanilino)propanoate Chemical compound C(C1=CC=CC=C1)(=O)N(C(C(=O)OCCCl)C)C1=CC=C(C=C1)F UKDPYBMPYKTMND-UHFFFAOYSA-N 0.000 description 1
- 241000209761 Avena Species 0.000 description 1
- 235000007319 Avena orientalis Nutrition 0.000 description 1
- YQVMVCCFZCMYQB-UHFFFAOYSA-N Flamprop Chemical compound C=1C=C(F)C(Cl)=CC=1N(C(C)C(O)=O)C(=O)C1=CC=CC=C1 YQVMVCCFZCMYQB-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 240000007594 Oryza sativa Species 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- 241000209140 Triticum Species 0.000 description 1
- 235000021307 Triticum Nutrition 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- 230000000895 acaricidal effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 238000005054 agglomeration Methods 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- KTYVHLCLTPLSGC-UHFFFAOYSA-N amino propanoate Chemical compound CCC(=O)ON KTYVHLCLTPLSGC-UHFFFAOYSA-N 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 238000006480 benzoylation reaction Methods 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000008033 biological extinction Effects 0.000 description 1
- 125000003917 carbamoyl group Chemical class [H]N([H])C(*)=O 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000000084 colloidal system Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000002361 compost Substances 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 238000012790 confirmation Methods 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 239000006184 cosolvent Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000004495 emulsifiable concentrate Substances 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 230000000855 fungicidal effect Effects 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 238000005470 impregnation Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 230000000749 insecticidal effect Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000008268 mayonnaise Substances 0.000 description 1
- 235000010746 mayonnaise Nutrition 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000013618 particulate matter Substances 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 231100000208 phytotoxic Toxicity 0.000 description 1
- 230000000885 phytotoxic effect Effects 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 239000013008 thixotropic agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/12—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by halogen atoms or by nitro or nitroso groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
この発明は穀物中の野性カラスムギを抑制する
ための新規な選択的除草剤に関するものである。
英国（U.K）特許明細書1164160には構造式：
の選択的除草性化合物について記載され、かつ特
許請求されている。ここでＲはハロゲン原子ある
いはアルキルまたはアルコキシ基を表わし、ｎは
０または１−５の整数で、ｎが１より大なる時は
各Ｒグループは同一かまたは異なつたものであ
る。R′はアルキレン基を表わし、R″はアルキ
ル、アルコキシ、アリールまたはアリールオキシ
アルキレン基を表わし、Ｙはカルボキシ基または
その塩あるいはエステル、または任意にモノーま
たはジ−Ｎ−置換されたカルバモイル基を表わ
す。
英国特許明細書1164160の化合物はコムギ中の
野生のカラスムギの抑制には良好な選択的除草性
を示すけれども、野生カラスムギ中と同様にオオ
ムギ中でも植物性毒性症候を示す傾向があるた
め、オオムギ中での使用は信頼性が低い。
密接に関連した化合物のグループが穀物、特に
オオムギ中の野生のカラスムギの抑制に対し、興
味ある選択性を有することが今や見い出された。
この発明によれば次の一般的な構造式：
を有する新規な化合物を提供する。ここでＲは塩
素および／またはフツ素；ｎは１または２；Ｙは
３個以下の炭素原子を含有し、そして少なくとも
１個のフツ素または塩素原子を含有するアルキル
またはアルケルニ基を表わす。
最良の結果を与える化合物は、たとえば（Ｒ）
ｎが３−クロロ−、４−クロロ、３−フルオロ、
４−フルオロ−、３，４−ジクロロ−、３，４−
ジフルオロ−、３−クロロ−４−フルオロ−、ま
たは３−フルオロ−４−クロロ−置換基を有する
る化合物の場合である。
Ｙに関しては、アルキルまたはアルケニル基が
直鎖または分岐鎖を有し、１から３個の炭素原子
を含有する。この発明の化合物はアルキル基Ｙ中
に少なくとも１個のフツ素および／または塩素原
子が存在することで特徴付けられ、一般的に云つ
て、１，２あるいは３個のかゝるハロゲン原子の
存在が満足な除草性を与える。２−クロロエチル
基が特に効果的である。
この発明の化合物は構造式：
の酸と適量のハロゲン化アルコールとを反応させ
ることよりなる方法により製造されうる。このエ
ステル化反応は適当なエステル化触媒、たとえば
硫酸などの無機酸あるいは、たとえばｐ−トルエ
ンスルホン酸などの有機酸の存在下で行いうる。
酸（）は種々の経路で製造され、簡単な例は適
当なアミノ酸エステルをベンゾイル化し、遊離酸
を分離するための加水分解することからなるもの
である。
穀物中の野生カラスムギに対して有用な選択的
活性を有するこの発明の化合物の具体例は：
２−クロロエチルＮ−ベンゾイル−Ｎ−（３，４
−ジクロロフエニル）−２−アミノプロピオネイ
ト、
２−クロロエチルＮ−ベンゾイル−Ｎ−（４−
フルオロフエニル）−２−アミノプロピオネイ
ト、２−クロロエチルＮ−ベンゾイル−Ｎ−（３
−クロロ−４−フルオロ−フエニル）−２−アミ
ノプロピオネイト、
これらの化合物は除草剤として既知の方法で使
用され、したがつてこの発明は活性成分としての
この発明の化合物と共に担体または界面活性剤ま
たは担体と界面活性剤の両方とからなる除草性組
成物を含む。同様に、この発明は耕作地に、この
発明の化合物または組成物の選択的除草量を適用
することから成る耕作地の穀物中の野生カラスム
ギの生長を抑制する方法にも関するものである。
ここで使用される用語「選択的除草量」とは、
野生カラスムギの生長を実質的に減少させ、同時
に穀物にわずかの植物性毒性を与えるに充分な化
合物または組成物量である。この化合物の選択的
除草性は以下の実施例に具体的に示される。
ここで使用する用語「担体」とは、無機あるい
は有機物で、合成または天然物から得られる固体
または液体を意味し、この担体と活性化合物は植
物、種子、土壌または処理さるべき他の目的物あ
るいはその貯蔵、運搬、取扱いに適するように混
合または配合される。
界面活性剤は乳化剤、分散剤または湿潤剤で、
それは非イオンでもイオン性でもよい。
通常、農薬の配合に適用される担体物質または
界面活性剤がこの発明の組成物に使用され、それ
らの中で適当な例はたとえば我々の有する英国特
許明細書第1289283または1164160号に見い出し得
る。
この発明の組成物は湿潤性粉末（Wettable
powder）、粉末（dust）、粒状物、溶液、乳化性
濃縮物、エマルジヨン、サスペンジヨン濃縮物お
よびエアロゾルとして配合される。湿潤性粉末は
通常25，50または75重量％の毒薬を含むように配
合され、また固体担体に加えて通常３−10重量％
の分散剤および必要なら０−10重量％の安定剤
（Stabilizer（ｓ））および／または他の添加剤た
とえばPenetrantsあるいはStickersを含有する。
粉末（dust）は通常湿潤性粉末の組成と類似の粉
末濃縮物（dust concentrate）として配合される
が分散剤を含まない。そしてこれは通常0.5−10
重量％の毒薬を含む組成物を与えるよう農地にお
いてさらに固体担体で希釈される。粒状物は通常
10と100BSメツシユの間の大きさ（1.676−0.152
mm）を有するよう製造され、凝集または注入
（impregnation）技術により生産される。
一般的に、粒状物は0.5−25重量％の毒薬と０
−10重量％の添加剤、たとえば安定剤、漸次放出
調節剤（Slow release modifier）および結合剤
を含む。乳化性濃俊物は溶剤および必要なら共溶
剤に加えて、通常10−50重量／容量％の毒薬、２
−20重量／容量％の乳化剤および0.20重量／容量
％の適当な添加剤たとえば安定剤、浸透剤および
防食剤を含有する。
サスペンジヨン濃縮物は安定な沈降性のない流
動性の生成物が得られるように混合され、通常10
−75重量％の毒薬、0.5−15重量％の分散剤たと
えば保護コロイドおよびチクソトロピツク剤など
の懸濁剤を0.1−10重量％、たとえば消泡剤、防
食剤、安定剤、浸透剤、固着剤などの適当な添加
剤を０−10重量％、および担体として毒薬が実質
的に不溶の水あるいは有機液体を通常含有する。
沈降するのを防ぐため、または水の氷結防止剤と
して担体中にある種の有機固体または無機塩が溶
解されうる。
たとえば、この発明の湿潤性粉末または濃縮物
を水で希釈することにより得られる組成物などの
水性分散液、エマルジヨンもこの発明の範囲内に
入る。このエマルジヨンはＷ／Ｏ型またはＯ／Ｗ
型で、濃厚な「マヨネーズ」様のコンシステンシ
ーを持ちうる。
この発明の組成物は、たとえば農薬、特に殺虫
性、殺ダニ性、除草性、殺菌性を有する化合物な
どの他の成分をも含有してもよい。
製造例 １
２−クロロエチルＮ−ベンゾイル−Ｎ−（３−
クロロ−４−フルオロフエニル）−２−アミノ
プロピオネイトの製法
Ｎ−ベンゾイル−Ｎ−（３−クロロ−４−フル
オロフエニル）−２−アミノプロピオン酸（3.215
ｇ、0.01モル）は２−クロロエタノール（25ml）
中に溶解される。そして無水塩化水素は６時間の
間撹拌溶液中に通じられる。混合物は100℃で３
時間加熱される。そして、溶媒は留去される。残
留物はエーテル（100ml）中に溶解されエーテル
溶液は重炭酸ナトリウム溶液と水で洗滌される。
エーテル層は分離され、乾燥され（Na2SO4）溶媒
留去し残留油を得、ヘキサンで処理すると２−ク
ロロエチル−Ｎ−ベンゾイル−Ｎ−（３−クロロ
−４−フルオロフエニル）−２−アミノプロピオ
ネイトの白色結晶（3.1ｇ、80％）、融点78−80℃
を得る。（実測値：C56.2；H4.2；Ｎ：3.6，
C18H16Cl2FNO3の理論値：C56.3，H4.2，N3.6
％）
製造例 ２−15
製造例１の化合物（化合物１）の場合と同じ方
法を用いて一連の化合物は製造される。化合物と
その物性の詳細は次の表に与えられる。
This invention relates to a new selective herbicide for controlling wild oats in grains. United Kingdom (UK) patent specification 1164160 has the structural formula: selective herbicidal compounds are described and claimed. Here, R represents a halogen atom or an alkyl or alkoxy group, n is 0 or an integer of 1-5, and when n is greater than 1, each R group is the same or different. R′ represents an alkylene group, R″ represents an alkyl, alkoxy, aryl or aryloxyalkylene group, and Y represents a carboxy group or a salt or ester thereof, or an optionally mono- or di-N-substituted carbamoyl group. Although the compound of British Patent Specification 1164160 shows good selective herbicidal properties for controlling wild oats in wheat, it tends to show phytotoxic symptoms in barley as well as in wild oats, so it is not suitable for use in barley. It has now been found that a group of closely related compounds have interesting selectivity for the suppression of wild oats in cereals, especially barley. According to this invention: The general structural formula of: Provided are novel compounds having the following properties. where R is chlorine and/or fluorine; n is 1 or 2; Y represents an alkyl or alkelni radical containing up to 3 carbon atoms and containing at least one fluorine or chlorine atom. Compounds giving the best results are for example (R)
n is 3-chloro-, 4-chloro, 3-fluoro,
4-fluoro-, 3,4-dichloro-, 3,4-
This is the case for compounds with difluoro-, 3-chloro-4-fluoro-, or 3-fluoro-4-chloro-substituents. For Y, the alkyl or alkenyl group has a straight or branched chain and contains 1 to 3 carbon atoms. The compounds of the invention are characterized by the presence of at least one fluorine and/or chlorine atom in the alkyl group Y, and generally the presence of 1, 2 or 3 such halogen atoms is Provides satisfactory herbicidal properties. The 2-chloroethyl group is particularly effective. The compound of this invention has the structural formula: acid and a suitable amount of halogenated alcohol. This esterification reaction may be carried out in the presence of a suitable esterification catalyst, for example an inorganic acid such as sulfuric acid, or an organic acid such as p-toluenesulfonic acid.
Acids () can be produced by various routes, a simple example consisting of benzoylation of the appropriate amino acid ester and hydrolysis to separate the free acid. Specific examples of compounds of this invention with useful selective activity against wild oats in cereals include: 2-chloroethyl N-benzoyl-N-(3,4
-dichlorophenyl)-2-aminopropionate, 2-chloroethyl N-benzoyl-N-(4-
fluorophenyl)-2-aminopropionate, 2-chloroethyl N-benzoyl-N-(3
-Chloro-4-fluoro-phenyl)-2-aminopropionate, these compounds are used in a known manner as herbicides and the invention therefore describes the use of carriers or surface-active compounds together with the compounds of the invention as active ingredients. Herbicidal compositions include both an agent or carrier and a surfactant. The invention likewise relates to a method for controlling the growth of wild oats in grains of cultivated land, which comprises applying to the cultivated land a selective herbicidal dose of a compound or composition of the invention. The term "selective herbicide amount" used here is
An amount of the compound or composition is sufficient to substantially reduce the growth of wild oats and at the same time impart slight phytotoxicity to the grain. The selective herbicidal properties of this compound are illustrated in the examples below. The term "carrier" as used herein means a solid or liquid, inorganic or organic, of synthetic or natural origin, in which the carrier and the active compound are present in the plant, seed, soil or other object to be treated or Mixed or formulated to suit its storage, transportation, and handling. Surfactants are emulsifiers, dispersants or wetting agents;
It may be non-ionic or ionic. Carrier substances or surfactants which are normally applied in the formulation of agrochemicals are used in the compositions of the invention, suitable examples of which can be found, for example, in our British Patent Specification No. 1289283 or 1164160. The composition of this invention is a wettable powder (wettable powder).
powder), dust, granules, solutions, emulsifiable concentrates, emulsions, suspension concentrates and aerosols. Wettable powders are usually formulated to contain 25, 50 or 75% by weight of poison, and usually 3-10% by weight in addition to the solid carrier.
of dispersants and optionally 0-10% by weight of stabilizers and/or other additives such as Penetrants or Stickers.
Dusts are usually formulated as dust concentrates similar in composition to wettable powders, but without dispersants. and this is usually 0.5−10
It is further diluted with a solid carrier in the field to give a composition containing % by weight of the poison. Particulate matter is usually
Size between 10 and 100BS mesh (1.676−0.152
mm) and produced by agglomeration or impregnation techniques. Generally, granules contain 0.5-25% by weight of poison and 0.
-10% by weight of additives such as stabilizers, slow release modifiers and binders. Emulsifying concentrates, in addition to the solvent and if necessary co-solvent, usually contain 10-50% w/v of the poison, 2
-20% w/v emulsifier and 0.20% w/v suitable additives such as stabilizers, penetrants and anticorrosion agents. Suspension concentrates are mixed to obtain a stable, non-sedimentable, fluid product and are typically mixed for 10 min.
- 75% by weight of poisonous agents, 0.5-15% by weight of dispersants, 0.1-10% by weight of suspending agents such as protective colloids and thixotropic agents, such as antifoaming agents, anticorrosion agents, stabilizers, penetrants, fixing agents, etc. 0-10% by weight of suitable additives, and as a carrier usually water or an organic liquid in which the poisonous drug is substantially insoluble.
Certain organic solids or inorganic salts may be dissolved in the carrier to prevent settling or as anti-icing agents for water. Also within the scope of this invention are aqueous dispersions, emulsions, such as, for example, compositions obtained by diluting the wettable powders or concentrates of this invention with water. This emulsion is W/O type or O/W type.
It can be molded and have a thick "mayonnaise"-like consistency. The compositions of the invention may also contain other ingredients, such as, for example, pesticides, especially compounds with insecticidal, acaricidal, herbicidal, and fungicidal properties. Production example 1 2-chloroethyl N-benzoyl-N-(3-
Process for producing chloro-4-fluorophenyl)-2-aminopropionate N-benzoyl-N-(3-chloro-4-fluorophenyl)-2-aminopropionic acid (3.215
g, 0.01 mol) is 2-chloroethanol (25 ml)
dissolved in Anhydrous hydrogen chloride is then passed into the stirred solution for 6 hours. The mixture is heated at 100℃
heated for an hour. The solvent is then distilled off. The residue was dissolved in ether (100 ml) and the ether solution was washed with sodium bicarbonate solution and water.
The ether layer was separated, dried (Na 2 SO 4 ) and evaporated to give a residual oil, which upon treatment with hexane gave 2-chloroethyl-N-benzoyl-N-(3-chloro-4-fluorophenyl)-2. - White crystals of aminopropionate (3.1 g, 80%), melting point 78-80°C
get. (Actual measurement value: C56.2; H4.2; N: 3.6,
Theoretical values of C 18 H 16 Cl 2 FNO 3 : C56.3, H4.2, N3.6
%) Preparation Example 2-15 A series of compounds are prepared using the same method as for the compound of Preparation Example 1 (Compound 1). Details of the compounds and their physical properties are given in the following table.
【表】【table】
【表】
試験例
選択的除草性確任試験（オオムギ中の野生カラ
スムギ）
オオムギ（var.Imbar）の25個の種子あるいは
野生カラスムギ（Avena Fatua）の30個の種子
は７cmのポツト中のJohn InnesNo.１堆肥に植付
けられる。植物が１１／２〜２１／２の葉期（leaf sta
ge）
に生長した時、ポツトは添加物として湿潤剤／固
着剤を含有している１：１アセトン／水混合物中
の試験中の化合物の溶液でスプレーされる。オオ
ムギは10から0.6Kg／haの投薬量で、野生カラス
ムギは2.0から0.15Kg／haの投薬量で処理され
る。各投薬は４回くり返される。ポツトは一日16
時間の投光（light）でほぼ21℃の温室に保たれ
る。評価はスプレー後10−14日後に行なわれる。
オオムギは土壌面で切断され、その重量は未処理
オオムギ重量のパーセンテージで表わされる。野
生カラスムギの生長の抑制割合は視覚的に評価さ
れる。この数字は生長禁止投薬量の計算に使用さ
れ、オオムギに10％減少（GID10）を与える投薬
量は野生カラスムギに90％減少（GID90）を与え
る投薬量と比較される。化合物の選択的因子は、
ＧＩＤ１０オオムギ／ＧＩＤ９０野生カラスムギ
で与えられる。
この試験の結果は次の表に示され、密接に関連
した化合物エチルＮ−ベンゾイル−Ｎ−（３，４
−ジクロロフエニル）−２−アミノプロピオネイ
トの結果が比較例として掲げられている。この対
照化合物は英国特許第1164160号明細書に開示さ
れているものである。該表において、GID10およ
びGID90はKg／haで表わされている。[Table] Test Example Selective herbicidal confirmation test (wild oat in barley) 25 seeds of barley (var.Imbar) or 30 seeds of wild oat (Avena Fatua) were placed in a 7 cm pot of John Innes No. .1 Planted in compost. The plant is in leaf stage from 11/2 to 21/2 (leaf sta
ge) When grown, the pots are sprayed with a solution of the compound under test in a 1:1 acetone/water mixture containing a wetting agent/fixing agent as an additive. Barley is treated at dosages of 10 to 0.6 Kg/ha and wild oats at dosages of 2.0 to 0.15 Kg/ha. Each dose is repeated four times. 16 pots per day
It is maintained in a greenhouse at approximately 21°C with hourly light. Evaluation is carried out 10-14 days after spraying.
Barley is cut at the soil level and its weight is expressed as a percentage of the untreated barley weight. The percentage inhibition of wild oat growth is visually assessed. This number is used to calculate the growth inhibiting dose, and the dose that causes a 10% reduction (GID 10 ) in barley is compared to the dose that causes a 90% reduction (GID 90 ) in wild oats. Compound selection factors are provided in GID 10 barley/GID 90 wild oat. The results of this test are shown in the following table and show the closely related compound ethyl N-benzoyl-N-(3,4
-dichlorophenyl)-2-aminopropionate is listed as a comparative example. This reference compound is that disclosed in GB 1164160. In the table GID 10 and GID 90 are expressed in Kg/ha.
【表】
この結果より、この発明の化合物は密接に関連
した化合物より選択性がよいことがわかる。
試験例
いくつかの化合物の除草活性をカラスムギ、イ
ネおよびとうもろこしに対して試験した実験結を
下記の表に示す。この葉面噴霧試験の評価につい
ては、０−９の植物毒性評価（０＝無影響、９＝
植物絶滅）を採用した。
これらのデータから、本発明による化合物は、
比較に用いた化合物よりも、雑草に対する高い活
性と穀物に対する低い植物毒性を一層良好に兼ね
備えている、ということがわかる。[Table] The results show that the compounds of this invention have better selectivity than closely related compounds. Test Example The results of experiments in which the herbicidal activity of several compounds were tested against oats, rice, and corn are shown in the table below. For the evaluation of this foliar spray test, a phytotoxicity rating of 0-9 (0 = no effect, 9 =
Plant extinction) was adopted. From these data, the compounds according to the invention:
It can be seen that it has a better combination of high activity against weeds and low phytotoxicity against grains than the compounds used for comparison.
【表】【table】
Claims (1)
１または２；Ｙは３個以下の炭素原子を含有し、
そして少なくとも１個のフツ素または塩素原子を
含有するアルキルまたはアルケニル基を表わ
す。〕 を有する化合物と担体あるいは界面活性剤または
担体と界面活性剤の両方を含有する、穀物中の野
性のカラスムギを抑制するのに適した除草性組成
物。[Claims] 1. The following general formula as an active ingredient: [wherein R is chlorine and/or fluorine; n is 1 or 2; Y contains up to 3 carbon atoms,
It also represents an alkyl or alkenyl group containing at least one fluorine or chlorine atom. ] A herbicidal composition suitable for controlling wild oats in grains, comprising a compound having the following formula and a carrier, a surfactant, or both a carrier and a surfactant.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB13088/74A GB1498411A (en) | 1974-03-25 | 1974-03-25 | 2-haloalkyl-aminopropionates and their use as selective herbicides |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS50160234A JPS50160234A (en) | 1975-12-25 |
| JPS6124361B2 true JPS6124361B2 (en) | 1986-06-10 |
Family
ID=10016622
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP50034586A Expired JPS6124361B2 (en) | 1974-03-25 | 1975-03-24 |
Country Status (13)
| Country | Link |
|---|---|
| JP (1) | JPS6124361B2 (en) |
| BE (1) | BE827046A (en) |
| CA (1) | CA1052386A (en) |
| CH (1) | CH616653A5 (en) |
| DD (1) | DD117333A5 (en) |
| DE (1) | DE2512940C2 (en) |
| ES (1) | ES435952A1 (en) |
| FR (1) | FR2265728B1 (en) |
| GB (1) | GB1498411A (en) |
| HU (1) | HU172883B (en) |
| IL (1) | IL46907A (en) |
| IT (1) | IT1049376B (en) |
| NL (1) | NL181163C (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS63172770U (en) * | 1987-04-30 | 1988-11-09 |
-
1974
- 1974-03-25 GB GB13088/74A patent/GB1498411A/en not_active Expired
-
1975
- 1975-03-04 CA CA221,216A patent/CA1052386A/en not_active Expired
- 1975-03-21 IT IT21527/75A patent/IT1049376B/en active
- 1975-03-24 IL IL46907A patent/IL46907A/en unknown
- 1975-03-24 DD DD184991A patent/DD117333A5/xx unknown
- 1975-03-24 CH CH375175A patent/CH616653A5/en not_active IP Right Cessation
- 1975-03-24 HU HU75SE00001774A patent/HU172883B/en not_active IP Right Cessation
- 1975-03-24 BE BE1006552A patent/BE827046A/en not_active IP Right Cessation
- 1975-03-24 ES ES435952A patent/ES435952A1/en not_active Expired
- 1975-03-24 NL NLAANVRAGE7503464,A patent/NL181163C/en not_active IP Right Cessation
- 1975-03-24 DE DE2512940A patent/DE2512940C2/en not_active Expired
- 1975-03-24 FR FR7509085A patent/FR2265728B1/fr not_active Expired
- 1975-03-24 JP JP50034586A patent/JPS6124361B2/ja not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS63172770U (en) * | 1987-04-30 | 1988-11-09 |
Also Published As
| Publication number | Publication date |
|---|---|
| AU7943175A (en) | 1976-09-30 |
| ES435952A1 (en) | 1976-12-16 |
| DE2512940C2 (en) | 1984-04-19 |
| DD117333A5 (en) | 1976-01-12 |
| IL46907A0 (en) | 1975-05-22 |
| NL181163B (en) | 1987-02-02 |
| GB1498411A (en) | 1978-01-18 |
| IT1049376B (en) | 1981-01-20 |
| NL7503464A (en) | 1975-09-29 |
| BE827046A (en) | 1975-09-24 |
| JPS50160234A (en) | 1975-12-25 |
| FR2265728B1 (en) | 1977-04-15 |
| FR2265728A1 (en) | 1975-10-24 |
| DE2512940A1 (en) | 1975-10-09 |
| NL181163C (en) | 1987-07-01 |
| HU172883B (en) | 1978-12-28 |
| IL46907A (en) | 1978-03-10 |
| CA1052386A (en) | 1979-04-10 |
| CH616653A5 (en) | 1980-04-15 |
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